反応 #44762

反応方程式

sodium bicarbonate

triethylamine

methyl 4-(bromomethyl)benzoate

N,N′-dimethylethan-1,2-diamine

→

methyl 4-[(methyl(2-(methylamino)ethyl)amino)methyl]benzoate

収率 62.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度to reflux for two hours
2. 2
   温度After cooling
3. 3
   抽出The mixture was extracted with ethyl acetate
4. 4
   洗浄The organic layer was washed with brine
5. 5
   乾燥dried over sodium sulfate
6. 6
   濃縮concentrated under reduced pressure

実験手順

A mixture of methyl 4-(bromomethyl)benzoate (2 g, 8.73 mmol) and N,N′-dimethylethan-1,2-diamine (7.5 mL, 70 mmol) was heated with triethylamine (9.8 mL, 70 mmol) in tetrahydrofuran (80 mL) to reflux for two hours. After cooling, the mixture was treated with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 1.28 g of methyl 4-[(methyl(2-(methylamino)ethyl)amino)methyl]benzoate, 1H NMR (300 MHz, CD3OD) δ 7.97 (d, 2H), 7.45 (d, 2H), 3.59 (s, 2H), 2.67 (m, 2H), 2.54 (m, 2H), 2.35 (s, 3H), 2.22 (s, 3H) ppm.

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